Understanding of Photo‐Induced Reversible Rearrangement from Borepin to Borirane

Zhu, Hongyang; Li, Quan-Song

doi:10.1002/chem.202201360

Cited by 6 publications

(1 citation statement)

References 84 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several theoretical studies on the PC reactions of AIEgens have stirred up extensive discussions. − Nakamura and colleagues studied the mechanism of the ring-closing reaction of 1,2-bis(3-thienyl)ethylene by calculating the conical intersection (CI) between the ground state (S 0 ) and the first excited state (S 1 ) . Su et al proposed that the PC reaction of diarylethene derivatives may occur in the excited state by scanning the potential energy surface of DAE PC by the TD-DFT method .…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Photocyclization Reaction-Induced Dual Aggregation-Induced Emission Phenomenon

Yang,

Wei,

et al. 2023

J. Phys. Chem. A

View full text Add to dashboard Cite

Photochromic molecules with aggregation-induced emission (AIE) effects are of great value and prospective in various practical applications. To explore its inherent mechanism, the open isomer ap-BBTE and the closed isomer c-BBTE were chosen to perform the theoretical calculation using the quantum mechanics/ molecular mechanics model combined with thermal vibration correlation function formalism. The calculations show that the photocyclization (PC) reaction from ap-BBTE to c-BBTE facilitates an improvement in the AIE effect. It is found that the fluorescence quantum yield (Φ F ) enhancement of ap-BBTE is attributed to the restriction of the low-frequency rotational motion of the benzothiophene moiety and the high-frequency stretching vibrations of the C−C bond between the benzothiophene and benzylbis(thiadiazole) vinyl groups after aggregation. For c-BBTE, the increase in Φ F upon aggregation is mainly due to the suppression of the high-frequency stretching vibration of the C−C bond between the benzothiophene and the benzobis(thiadiazole) vinyl groups. In addition, the AIE effect was also enhanced from ap-BBTE to c-BBTE, which is consistent with the experimental phenomenon. The corresponding emission spectrum red-shifted from ap-BBTE to c-BBTE in both dilute solution and the crystalline state due to the improved intramolecular conjugation of c-BBTE. Moreover, the PC reaction from ap-BBTE to c-BBTE easily occurs in an excited state with a low energy barrier transition state by forming a C−C bond between benzothiophene groups effectively in dilute solution. Our calculations provide theoretical guidance for the further rational design of efficient AIE luminogens.

show abstract

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Photocyclization Reaction-Induced Dual Aggregation-Induced Emission Phenomenon

Yang,

Wei,

et al. 2023

J. Phys. Chem. A

View full text Add to dashboard Cite

show abstract

Photoresponsive Drug Delivery Systems: Challenges and Progress

Yang,

Long,

Chu

et al. 2024

Adv Funct Materials

View full text Add to dashboard Cite

Photoresponsive drug delivery systems (PDDSs) have emerged as a promising toolbox for drug delivery, offering precise control over the site, duration, and dosage of light‐triggered medication. It allows controlled drug release, photo‐triggered targeting, diagnosis, and treatment, improving the precision and efficacy of therapies for various diseases. Despite progress in designing different PDDSs, clinical translation has been limited due to various obstacles. Herein, this review article focuses on three critical challenges of PDDSs: 1) accumulation at diseased lesions, 2) precision of light irradiation, and 3) penetration of light in tissues. Also, this article summarizes and discusses current advancements and strategies to address these challenges. Overall, it emphasizes the need to clarify the current challenges from bench to bedside and develop strategies to enhance therapeutic outcomes, increase compatibility and patient compliance, and unlock the possibilities in different clinical therapies.

show abstract

Borirenes and Boriranes: Development and Perspectives

Wang,

2023

Chemistry A European J

View full text Add to dashboard Cite

Strained compounds constitute a highly topical area of research in chemistry. Borirene and borirane both feature a BC2 three‐membered ring. They can be viewed as the structural analogues of cyclopropane and cyclopropene, where a CH2 unit of the carbonaceous counterparts is replaced with BH, respectively. Indeed, this structural variation introduces numerous intriguing aspects. For instance, borirane and borirene are both Lewis acidic due to the presence of a tricoordinate borane center. In addition, borirene is 2π aromatic according to Hückel's rule. In addition to their ability to form adducts with Lewis bases and the capacity of borirenes to act as ligands in coordination with metals, both borirenes and boriranes exhibit ring‐opening reactivity due to the considerable ring strain. Under specific conditions, coordinated boriranes can even cleave two BC bonds to serve as formal borylene sources (although the reaction mechanisms are quite complex). On the other hand, recent successful syntheses of benzoborienes and their carborane‐based three‐dimensional analogues (also referred to as carborane‐fused boriranes) have introduced novel perspectives to this field. For instance, they display excellent ring‐expanding reactivity, possibly attributed to the boosted ring strain arising from the fusion of borirenes with benzene and boriranes with o‐carborane. Importantly, their applications as valuable “BC2” synthons have become increasingly evident along with the newly disclosed reactivity. Additionally, the boosted Lewis acidity of carborane‐fused boriranes, thanks to the potent electron‐withdrawing effect of o‐carborane, combined with their readiness for ring enlargement, makes them promising candidates as electron‐accepting building blocks in the construction of chemically responsive luminescent materials. This review provides a summary of the synthesis and reactivity of borirene and borirane derivatives, with the aim of encouraging the design of new borierene‐ and borirane‐based molecules and inspiring further exploration of their potential applications.

show abstract

Understanding of Photo‐Induced Reversible Rearrangement from Borepin to Borirane

Cited by 6 publications

References 84 publications

Theoretical Study of the Photocyclization Reaction-Induced Dual Aggregation-Induced Emission Phenomenon

Theoretical Study of the Photocyclization Reaction-Induced Dual Aggregation-Induced Emission Phenomenon

Photoresponsive Drug Delivery Systems: Challenges and Progress

Borirenes and Boriranes: Development and Perspectives

Contact Info

Product

Resources

About